2,2,5,5-tetramethyl-4-phenyl-3-azahexane-3-nitroxide | 53544-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,5,5-tetramethyl-4-phenyl-3-azahexane-3-nitroxide
• CAS: 53544-93-7
• 化学式: C₁₅H₂₄NO
• 分子量: 234.362
• InChiKey: WIWNROIMXYHLMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  4.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,5,5-tetramethyl-4-phenyl-3-azahexane-3-nitroxide 、 (1-溴乙基)苯 在 肼 、 lead dioxide 作用下， 以 甲苯 为溶剂， 以59%的产率得到2,2,5,5-tetramethyl-3-(1-phenylethoxy)-4-phenyl-3-azahexane
  参考文献：
  名称：

  手性无环氮氧化物与前手性自由基偶联的立体化学研究

  摘要：

  摘要 研究了一系列在与氮氧氮相邻的碳上带有一个氢原子的无环手性氮氧化合物在与前手性基团 1-苯乙基的偶联反应中的立体选择性。在一个案例中，获得了主要非对映异构体的 X 射线结构，这证实了预测立体选择性的模型。

  DOI：

  10.1081/scc-120039497
• 作为产物：
  描述：

  N-叔丁基-α-苯基硝酮 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 0.28h， 生成 2,2,5,5-tetramethyl-4-phenyl-3-azahexane-3-nitroxide
  参考文献：
  名称：

  Stable nitroxyl radicals with a hydrogen atom at ?-carbon atom of nitroxyl group

  摘要：

  Nitroxyl radicals containing the diphenylmethyl group as one of the substituents at the nitroxyl group are stable compounds that can be isolated in an individual state. N-(2-Hydroxy-3-methyl-2-phenylcyclohexyl)-N- diphenylmethylnitroxyl was characterized by X-ray diffraction analysis for the first time.

  DOI：

  10.1007/bf01433978

文献信息

• Development of a Universal Alkoxyamine for “Living” Free Radical Polymerizations
  作者：Didier Benoit、Vladimir Chaplinski、Rebecca Braslau、Craig J. Hawker

  DOI：10.1021/ja984013c

  日期：1999.4.1

  “living” or controlled polymerization of a wide range of vinyl monomers. Surveying a variety of different alkoxyamine structures led to α-hydrido derivatives based on a 2,2,5-trimethyl-4-phenyl-3-azahexane-3-oxy, 1, skeleton which were able to control the polymerization of styrene, acrylate, acrylamide, and acrylonitrile based monomers. For each monomer set, the molecular weight could be controlled from 1000

  对新型烷氧基胺的研究表明，硝基氧在介导各种乙烯基单体的“活性”或受控聚合方面发挥着关键作用。调查各种不同的烷氧基胺结构导致基于 2,2,5-trimethyl-4-phenyl-3-azahex-3-oxy, 1, 骨架的 α-氢化衍生物能够控制苯乙烯、丙烯酸酯的聚合、丙烯酰胺和丙烯腈基单体。对于每个单体组，分子量可以控制在 1000 到 200 000 amu 之间，多分散性通常为 1.05-1.15。基于上述单体的组合的嵌段和无规共聚物也可以用类似的控制来制备。与 2,2,6,6-四甲基哌啶氧基 (TEMPO) 相比，这些新系统代表了可在受控条件下聚合的单体范围的显着增加，并克服了与氮氧化合物介导的“活性”自由基程序相关的许多限制。单体选择和功能...
• An ESR and HPLC-EC Assay for the Detection of Alkyl Radicals
  作者：Christo P. Novakov、Dennis Feierman、Arthur I. Cederbaum、Detcho A. Stoyanovsky

  DOI：10.1021/tx015507h

  日期：2001.9.1

  The correlation of lipid peroxidation with release of alkanes (RH) is considered a noninvasive method for the in vivo evaluation of oxidative stress. The formation of RH is believed to reflect a lipid hydroperoxide (LOOH)-dependent generation of alkoxyl radicals (LO.) that undergo, beta -scission with release of alkyl radicals (R-.). Alternatively, R-. could be spin-trapped with a nitrone before the formation of RH and analyzed by ESR. Extracts from the liver and lung of CCl4- and asbestos-treated rats that were previously loaded with nitrones exhibited ESR spectra suggesting the formation of iso-propyl, n-butyl, ethyl, and pentyl radical-derived nitroxides. In biological systems, various nitroxides with indistinguishable ESR spectra could be formed. Hence, experiments with N-tert-butyl-alpha -phenylnitrone (PBN) for spin trapping of R-. were carried out in which the nitroxides formed were separated and analyzed by HPLC with electrochemical detection (EC). The C1-5 homologous series of PBN nitroxides and hydroxylamines were synthesized, characterized by ESR, GC-MS, and HPLC-EC, and used as HPLC standards. For in vivo generation and spin trapping of R-., rats were loaded with CCl4 and PBN. The HPLC-EC chromatograms of liver extracts from CCl4-treated rats demonstrated the formation of both the nitroxide and hydroxylamine forms of PBN/(CCl3)-C-., as well as the formation of a series of unidentified PBN nitroxides and hydroxylamines. However, formation of PBN adducts with retention times similar to these of the PBN/C2-5 derivatives was not observed. In conclusion, we could not correlate the production of PBN-detectable alkyl radicals with the reported CCl4-dependent production Of C1-5 alkanes. We speculate that the major reason for this is the low steady-state concentrations of R-. produced because only a small fraction of LO. undergo,beta -scission to release R-..
• Abe, Yukino; Seno, Shin-ya; Sakakibara, Kazuhisa, Journal of the Chemical Society. Perkin transactions II, 1991, # 6, p. 897 - 903
  作者：Abe, Yukino、Seno, Shin-ya、Sakakibara, Kazuhisa、Hirota, Minoru

  DOI：——

  日期：——
• Rate constants for addition of triethylsilyl radicals to spin traps
  作者：R. G. Gasanov、L. V. Ivanova、R. Kh. Freidlina

  DOI：10.1007/bf00947858

  日期：1984.4
• Stable nitroxyl radicals with a hydrogen atom at ?-carbon atom of nitroxyl group
  作者：V. A. Reznikov、I. A. Gulorov、Yu. V. Gatilov、T. V. Rybalova、L. B. Volodarsky

  DOI：10.1007/bf01433978

  日期：1996.2

  Nitroxyl radicals containing the diphenylmethyl group as one of the substituents at the nitroxyl group are stable compounds that can be isolated in an individual state. N-(2-Hydroxy-3-methyl-2-phenylcyclohexyl)-N- diphenylmethylnitroxyl was characterized by X-ray diffraction analysis for the first time.